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Mild Synthesis of Substituted 1,2,5-Oxadiazoles Using 1,1'-Carbonyldiimidazole as a Dehydrating Agent

Andrew J. Neel* and Ralph Zhao

*Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States, Email:

A. J. Neel, R. Zhao, Org. Lett., 2018, 20, 2024-2027.

DOI: 10.1021/acs.orglett.8b00568 (free Supporting Information)

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1,1'-Carbonyldiimidazole induces the formation of various 3,4-disubstituted 1,2,5-oxadiazoles (furazans) from the corresponding bisoximes at ambient temperature. This method enables the prepartion of these inherently energetic compounds at temperatures well below their decomposition points and with improved functional group compatibility.

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ID: J54-Y2018